This invention relates to the aralkoxy, alkoxy, alkadienyloxy and alkenyloxy-1,3,2-dioxaborinane derivatives having the structure: ##STR2## (wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different hydrogen, methyl and ethyl; and wherein R represents C.sub.6 straight chain alkenyloxy; C.sub.10 branched chain alkenyloxy; C.sub.12 aralkoxy; C.sub.12 branched chain alkoxy; or C.sub.10 branched chain alkadienyloxy) and uses thereof in augmenting or enhancing the aroma of perfumed compositions including but not limited to drier-added fabric softener articles, fabric softener compositions and solid or liquid anionic, cationic, nonionic or zwitterionic detergents and perfumed polymers.
Materials which can provide various aromas, e.g., floral, rose, citrusy, muguet, fresh air, ozoney, woody, piney, camphoraceous, leafy and green aromas with muguet, rose, floral, citrusy, herbaceous, green, woody, peppery and straw-like undertones when contacted with water or water vapor are highly desirable in the art of perfumery and in the fabric softener and detergent art. Such substances in the past have not been commercially useful in view of the fact that residues of the aroma imparting substance are left on the articles to be perfumed or on the articles to be deodorized using such perfumery substances.
The use of boric acid esters in perfumery has heretofore not been disclosed in the prior art except for use as intermediates in the synthesis of chemicals useful in augmenting or enhancing the aroma of perfume compositions and perfumed articles.
Thus, the borate ester of 3-endo-methyl-3-exo(4'-methyl-5'-hydroxypentyl)norcamphor is shown as an intermediate for producing dihydro-beta-santalol in U.S. Pat. No. 3,662,007 issued on May 9, 1972.
However, arylalkanol esters of boric acid and glycol borates are shown to be useful for killing bacteria and fungi in U.S. Pat. No. 3,564,091 issued on Feb. 16, 1971. Indeed, the compound having the structure: ##STR3## is shown to be useful in said U.S. Pat. No. 3,564,091 issued on Feb. 16, 1971 and the preparation of this compound is set forth at column 4, lines 35-48 of U.S. Pat. No. 3,564,091 the specification for which is incorporated by reference herein.
This compound is shown to be useful in the perfumery art in my copending application for U.S. Letters Patent, Ser. No. 073,289 filed on July 14, 1987.
The use as a precursor of the genus defined according to the structure: ##STR4## wherein A is an aryl hydrocarbon group of 5-14 carbon atoms and R is an aliphatic hydrocarbon group of more than one carbon atom and the compound: ##STR5## may be phenylethyl alcohol is set forth at lines 40-52, at column 1 of U.S. Pat. No. 3,564,091, to wit:
"More particularly, this invention relates to the use as biocides, compounds selected from the group consisting of (1) esters of boric acid and an alcohol of the formula A--R--OH, wherein A is an aryl hydrocarbon group of 5-14 carbon atoms and R is an aliphatic hydrocarbon group of more than one carbon atom, and (2) A--R--OH alcohol esters of glycol orthoborates wherein A and R are as described above. PA0 In the general formula above, A is preferably selected from the group consisting of phenyl, naphthyl, phenanthracyl, and anthracyl. The glycol is selected from the group consisting of alpha and beta glycols containing 3-20 carbon atoms. The term boric acid embraces ortho-, meta-, and pyroboric acids, and boric oxide." PA0 "wherein each R represents the same or different member of the group consisting of hydrogen and monovalent hydrocarbon radicals including alkyl, cycloalkyl, aryl, aralkyl and alkaryl groups, and R' represents a monovalent hydrocarbon radical including alkyl, cycloalkyl, aryl, aralkyl and alkaryl groups").
U.S. Pat. No. 2,839,564 issued on June 17, 1958; U.S. Pat. No. 2,940,839 issued on June 14, 1960; and U.S. Pat. No. 3,189,637 issued on June 15, 1965 as well as United Kingdom Patent Specification No. 722,538 published on Jan. 26, 1955 each disclose borate esters having the generic structure: ##STR6## wherein R.sub.11, R.sub.12, R.sub.13 and R.sub.14 can represent hydrogen or alkyl and R.sub.15 represent various hydrocarbon moieties (for example the definition of the R moieties at column 1, lines 29-34 of U.S. Pat. No. 2,839,564 states:
The borate esters having the generic structure: ##STR7## as disclosed in the aforementioned Patents and U.K. Patent Specification are indicated to be useful in causing fuel to be made more efficient on operation of internal combustion engines by reduction of octane requirements.
The prior art does not set forth explicitedly or implicitedly the use of such a genus or members of such a genus in perfumery or in perfumed articles or perfumed polymers.
U.S. Pat. No. 4,391,999 issued on July 5, 1983 entitled: "3,4,5,6,6-PENTAMETHYL HEXANOL-2- AND ALKYL HOMOLOGUES THEREOF; PROCESS FOR PREPARING SAME AND ORGANOLEPTIC USES THEREOF" on which I am the inventor, discloses the compound having the structure: ##STR8## as being useful in augmenting or enhancing the aroma of perfumed compositions and perfumed articles.
The publication "Perfume and Flavor Chemicals (Aroma Chemicals)", Volume I, by Steffen Arctander (1969) discloses the usefulness of the compounds having the structure: ##STR9## in augmenting or enhancing the aroma of perfume compositions at, inter alia, Monographs 1427 and 669.
Nothing in the prior art discloses the aralkoxy, alkoxy, alkadienyloxy and alkenyloxy-1,3,2-dioxaborinane derivatives defined according to the structure: ##STR10## (wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different hydrogen, methyl and ethyl; and wherein R represents C.sub.6 straight chain alkenyloxy; C.sub.10 branched chain alkenyloxy; C.sub.12 aralkoxy; C.sub.12 branched chain alkoxy; or C.sub.10 branched chain alkadienyloxy).
Furthermore, nothing in the prior art discloses the aralkoxy, alkoxy, alkadienyloxy and alkenyloxy-1,3,2-dioxaborinane derivatives generically as being useful in augmenting or enhancing the aroma of perfume compositions, perfumed articles and perfumed polymers.